If you are looking for lunch in Winter Park, try Rose's Mountain Cafe. As you head through town from Grand Lake, it will be on your right, a small stand-alone bungalow type building. Excellent food and ambiance. Or, for fabulous pizza, go to Hernando's.

Just remember that Bradley Boulder includes breakfast so you might not want to go out for breakfast on Friday.

I (wife) am wondering about the "trekking poles". How necessary are these? Would we be better off waiting until we get to Denver to purchase them? As far as clothing goes, I understand that we need to layer but can someone give me an example? Living in Houston doesn't give us much of an opportunity to layer. My concern is ... shorts? capris? jeans? pants? not real sure what is appropriate. I am thinking that it is going to feel somewhat "cool" there after leaving the 90-100 degree weather. I know the sun is strong, but that doesn't necessarily mean heat. I hope these questions make sense to someone. My husband is quite comfortable wearing shorts year round...I on the other hand am somewhat cold natured. Thanks for all your help and advice.

Probably not shorts and not jeans because if they get wet they take forever to dry. I don't like them, but there are those convertible pants that zip off /on for shorts/pants. Something that dries quickly and has a number of pockets usually works best. Try Eddie Bauer, REI, Columbia, Patagonia or any number of sports outfitters. They all have plenty to select from and in a variety of price ranges.

As to layering, a T-shirt or long sleeve shirt, plus another sweater and a rain jacket for the basics. Carry another sweater or warmer top in back pack. If you go to REI and there is one in Denver at the Confluence, near Lodo/downtown, they will be able to point you in the right direction towards the items that will work best for you and your activities. Personally I'd wait and shop in Denver (REI).

Good questions! I'd say play it by ear on how long to stay on Sunday in Boulder. See if you can find some info on the hikes in the Boulder mountain parks in advance - there are some lovely short ones so maybe you could do one early then head out. I forgot to mention Chautauqua - lovely place with a nice breakfast. I guess they do lunch & dinner too I've just only had bfst. They also have some concerts & other programs so would google to check that out in advance because it's lovely there.
Raton is a wide spot on I-25 (I'll just apologize now for any residents/fans that this offends) and not much more. Trinidad is way cuter - kind of an old west town with the added distinction of being America's sex change capital
On layering. Think base layer, warm layer, waterproof layer. When I hike I avoid cotton entirely - to historytraveler's point, it takes forever to dry & if you get wet you will get cold fast. I think REI is the best outdoor store too & you must have some in Houston. Their employees are knowledgeable about their products and the outdoors. If I'm doing a short (<5 mile) hike, I probably wear a base layer & carry only a waterproof layer. so probably a (non-cotton) tshirt & carry my rain jacket. If you're doing a long hike, I'd wear a T and carry both a fleece & a rain jacket in my pack. you'll also find that you might be cold when you start & warm up quickly as you climb, then be cold at the top where there's more wind - you'll be on & off with the layers like crazy!
i love the convertible pants, but if you tend to be cold you would also be perfectly happy with hiking pants that aren't convertible (something made of nylon blend vs cotton). REI will have a selection of many different brands. If you're comfortable in Houston you're not likely to get hot in CO except in the city where you can where your cute normal clothes!
If you don't already have some of this "techwear," REI's a great place to shop because they have everything. Since you're runners, you may already have some synthetic tshirt & that's fine.
i have trekking poles, and they're a great relief on very steep hikes. unless you have bad knees, i wouldn't say it's worth a purchase for other hikes. it doesn't really make sense to rent them at REI in denver because you'd have them for several days before you get back & at that point you could have bought a pair. i just don't think you're likely to do anything all that steep anyway.
Wow, you're making me miss Colorado!

I've hiked quite a lot in RMNP and have never used trekking poles so don't think they are necessary. It could be one of those things that once you've tried it you'll never go back - but I don't know. There are certainly a lot of people who manage quite well without them.

Layering - For hiking in RMNP in summer I wear capris and a t-shirt with either a long-sleeved t-shirt or a light-weight fleece to put over the t-shirt, depending on what the weather report is. I also have a gore-tex rain jacket. You really need some sort of rain gear - even if it's just cheapo ponchos.

For shoes it depends on the hike - for something easy (ie, Lulu city) I wear my keen sandles, intermediate sneakers and hard I put on the boots. If you're going on quite a long hike it's not a bad idea to put a spare pair of socks in your pack. If you do get caught in some rain your feet will invariable get wet and once the rain stops there's very little better than putting on some dry socks.

I usually put a few spare ziploc bags in my pack in case I run into a real storm I can put camera/wallet etc in them as my pack isn't completely water-proof.

Speaking of packs - if you don't already have a good day pack you might want to stop in at REI in Denver and pick one up. Mine is a camel back so it has a big pouch for water with a hose that comes around to the front to drink out of. I love this because I can get a drink whenever I want (which is quite often) without having to carry a bottle or stop to get it out of the pack.

hth

Somehow I forgot to mention that fleece is a better alternative to a sweater.

As to your question regarding the necessity of trekking poles...no, they are not necessary. They can be helpful. IMO they are only useful if doing a lot of uphill hiking, hiking over rough terrain or if you have difficulty walking.

I wouldn't bother with them unless you can rent them cheaply or buy on sale.

again great suggestions......fleece shirts in, trekking poles out.